a- AND 0-BENZALDOXIMES 197
(Cc*^^ ':I 2> separate out, which may be recrystallised from
spiri^ s« y
*C,.Lv---------.2NH3 = (CGH5CH),N2+3H20.
J-t ont Qrx tjie Water-bath 2 c.c. benzaldehyde and 2 c.c.
to i ex^ hour. Crystals of benzalaniline are formed
iig-5 C(iHL3COH + C0H5NH2 = C0HSCH:N.C0H3 -f H2O,
mo.y bci filtered and crystallised from spirit ; m. p. 42°.
*t*cc llp> together 10 grams of benzaldehyde with 9 grams
x3OtilsH in 6 c.c. of water until a permanent emulsion is
z\.nd lGt stand 3—4 hours. Dissolve the solid product in
a littlo xviitof and shake out with ether twice. On acidifying
the a.cj[i.ioou.s -portion with hydrochloric acid, benzoic acid is
precipit-rxtecl. jriiter and wash with a little cold water and dry.
Distil tlic Gtlaer from the ethereal solution. The residue
is benzyl ;UCoi-ol (Cannizzaro).
3C:ttHrtCo H + KOH = C6H6COOK + CflH3CH2OH.
ctlso Ueactions on p. 135 and p.1 174, and Appendix ^ p. 300.
«- and-0-Benzaldoximes, C0H6CH:NOH
Beckmann, Ber.9 1890, 23, 1684.
1 5 yy hydroxylamine hydrochlori-de.
*4 yy caustic soda (in 40 c.c. water).
Tlio ssolution of caustic soda and benzaldehyde are mixed and
the liyclroxylfxrnine hydrochloride gradually added with constant
sha1cii™i|4". Hie liquid becomes slightly warm and the oil even-
tu-aily dissolves, forming a yellow solution which has lost the
smell of toenza-lclehyde. On cooling, a crystalline mass of the
hydrocliloride of benzaldoxime separates. Sufficient water is
added, to form, a clear solution, through which a current of
carbon dioxide is passed. A colourless emulsion of the a- or
#;z//-£xlcloxime separates on the surface and is extracted with
ethei", dehydrated over anhydrous sodium sulphate and the
ether rcMiiovod on the water-bath. Impure benzcz^//aldoxime
remn-iiiH and is purified as follows. It is poured into a
satuiTLtcsd soli_ition of sodium ethoxide in alcohol (prepared by
dissolving 5 |>'i*a,ms sodium in 60 c.c. alcohol), when the aldoxime